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Molecules 2012, 17(4), 3969-3980; doi:10.3390/molecules17043969

Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives

1
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education,Guangzhou 510642, China
2
Laboratory of Insect Toxicology, South China Agricultural University, Guangzhou 510642, China
*
Author to whom correspondence should be addressed.
Received: 15 February 2012 / Revised: 15 March 2012 / Accepted: 22 March 2012 / Published: 2 April 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

Based on the original structure of harmine, several novel 1,2,3,4-tetrahydro-β-carboline, β-carboline and 1-substituted-β-carboline derivatives bearing a substituted carbohydrazide group at C-3 were designed and synthesized to investigate the structure-activity relationship of their analogues. All of the compounds were characterized by infrared (IR), proton and carbon nuclear magnetic resonance (1H-NMR, 13C-NMR), and mass spectroscopy (MS). The bioassay tests showed that N'-benzylidene-1-phenyl-β-carboline-3-carbohydrazide (C25H18N4O, m.w. 390.4) (c2) and N'-(4-trifluoromethyl-benzylidene)-1-phenyl-β-carboline-3-carbohydrazide (C26H17N4OF3, m.w. 458) (d2) exhibited good inhibitory activity against dicotyledonous and monocotyledonous weeds, with EC50 values of 4.83 µM and 14.25 µM, respectively.
Keywords: N'-substituted-1,2,3,4-β-tetrahydro-β-carboline-3-carbohydrazide; β-carboline; N'-substituted-β-carboline-3-carbohydrazides; 1-substituted-β-carboline-3-carbohydrazides; herbicidal activity N'-substituted-1,2,3,4-β-tetrahydro-β-carboline-3-carbohydrazide; β-carboline; N'-substituted-β-carboline-3-carbohydrazides; 1-substituted-β-carboline-3-carbohydrazides; herbicidal activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Weng, Q.; Huang, J.; Zeng, Y.; Deng, Y.; Hu, M. Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives. Molecules 2012, 17, 3969-3980.

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